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The title compound, C21H18O2, crystallized in the centrosymmetric space group P21/n with one mol­ecule in the asymmetric unit. There is a single hydrogen bond, with an Odonor...Oacceptor distance of 2.624 (2) Å, which forms a cyclic dimer about a center of symmetry. The carboxyl group O atoms are ordered, while the carboxyl-H atom is disordered. A single leading intermolecular C—H...O interaction has an H...O distance of 2.68 Å and a C—H...O angle of 178°; this interaction forms chains. Taken together with the hydrogen bond, it generates chains and rings. Structural comparisons are made with trans-cinnamic acid and with 4-methyl-trans-cinnamic acid.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100002778/fr1261sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100002778/fr1261Isup2.hkl
Contains datablock I

CCDC reference: 146050

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN and PLATON (Spek, 1990).

(I) top
Crystal data top
C21H18O2F(000) = 640
Mr = 302.37Dx = 1.218 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 16.942 (1) ÅCell parameters from 25 reflections
b = 5.932 (2) Åθ = 13.2–17.4°
c = 17.265 (1) ŵ = 0.08 mm1
β = 108.122 (5)°T = 296 K
V = 1649.2 (5) Å3Cut column, colorless
Z = 40.38 × 0.19 × 0.15 mm
Data collection top
Rigaku AFC5S
diffractometer
Rint = 0.043
Radiation source: X-ray tubeθmax = 27.6°, θmin = 2.0°
Graphite monochromatorh = 022
ω scansk = 07
3942 measured reflectionsl = 2221
3816 independent reflections6 standard reflections every 150 reflections
1452 reflections with I > 2.00σI intensity decay: + 1.6 (average maximum relative intensity)
Refinement top
Refinement on F2216 parameters
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.057Weighting scheme based on measured s.u.'s 1/[σ2cs + (0.004 I)2]
wR(F2) = 0.073(Δ/σ)max = 0.0003
S = 1.36Δρmax = 0.54 e Å3
3816 reflectionsΔρmin = 0.49 e Å3
Special details top

Experimental. The Laue group assignment, the systematic absences and the centrosymmetry indicated by the intensity statistics led to assignment of the space group uniquely as P21/n (No. 14); since refinement proceeded well, it was adopted. Fourier difference methods were used to locate initial H atom positions, excepting the carboxyl H atom, and these H atoms were refined. Refined C—H distances ranged from 0.92 (3) to 1.13 (3) Å, with mean value 1.02 (5) Å; their Uiso values ranged from 0.9 to 1.6 times the Ueq values of the attached C atoms. The H atoms, excepting the carboxyl H atom, H7 and H8 were then made canonical, with C—H = 0.98 Å and Uiso = 1.2 × Ueq of the attached C atom. In the later stages of refinement the extinction coefficient was predicted to be negative, so was not included in the model. The maximum peak in the final difference map occurs ~0.9 Å from O1, but not in a position to be interpretable as a carboxyl H atom, while the maximum negative peak occurs ~1.8 Å from C21 and 2.0 Å from C15 and C16.

Geometry. Table of Least-Squares Planes ——————————

————– Plane number 1 —————

Atoms Defining Plane Distance e.s.d. O1 (1) 0.0000 O2 (1) 0.0000 C9 (1) 0.0000

Mean deviation from plane is 0.0000 angstroms Chi-squared: 0.0

————– Plane number 2 —————

Atoms Defining Plane Distance e.s.d. C9 (1) 0.0228 0.0028 C8 (1) -0.0179 0.0029 C7 (1) -0.0219 0.0027 C1 (1) 0.0162 0.0023

Additional Atoms Distance H1 (1) 0.2052 H2 (1) 0.1776

Mean deviation from plane is 0.0197 angstroms Chi-squared: 209.3

Dihedral angles between least-squares planes plane plane angle 2 1 3.35

————– Plane number 3 —————

Atoms Defining Plane Distance e.s.d. C1 (1) -0.0066 0.0023 C2 (1) 0.0105 0.0025 C3 (1) -0.0040 0.0026 C4 (1) -0.0069 0.0026 C5 (1) 0.0081 0.0023 C6 (1) -0.0022 0.0023

Additional Atoms Distance C10 (1) 0.0204 C11 (1) 0.0421 C7 (1) -0.0100 C8 (1) -0.4658 C9 (1) -0.3400 O1 (1) 0.2345 O2 (1) -0.7880

Mean deviation from plane is 0.0064 angstroms Chi-squared: 44.6

Dihedral angles between least-squares planes plane plane angle 3 1 28.26 3 2 27.05

————– Plane number 4 —————

Atoms Defining Plane Distance e.s.d. C12 (1) -0.0267 0.0021 C13 (1) -0.0177 0.0023 C14 (1) 0.0205 0.0026 C15 (1) 0.0198 0.0027 C16 (1) -0.0252 0.0030 C17 (1) -0.0337 0.0032 C18 (1) 0.0138 0.0029 C19 (1) 0.0311 0.0025 C20 (1) 0.0138 0.0022 C21 (1) 0.0035 0.0024

Mean deviation from plane is 0.0206 angstroms Chi-squared: 817.0

Dihedral angles between least-squares planes plane plane angle 4 1 69.98 4 2 67.51 4 3 80.54

————– Plane number 5 —————

Atoms Defining Plane Distance e.s.d. C1 (2) 0.0066 0.0023 C2 (2) -0.0105 0.0025 C3 (2) 0.0040 0.0026 C4 (2) 0.0069 0.0026 C5 (2) -0.0081 0.0023 C6 (2) 0.0022 0.0023

Mean deviation from plane is 0.0064 angstroms Chi-squared: 44.6

Dihedral angles between least-squares planes plane plane angle 5 1 76.04 5 2 73.94 5 3 89.64 5 4 10.29

————– Plane number 6 —————

Atoms Defining Plane Distance e.s.d. C12 (1) -0.0077 0.0021 C13 (1) -0.0045 0.0023 C14 (1) 0.0129 0.0026 C15 (1) -0.0025 0.0027 C20 (1) 0.0173 0.0022 C21 (1) -0.0137 0.0024

Mean deviation from plane is 0.0098 angstroms Chi-squared: 122.6

Dihedral angles between least-squares planes plane plane angle 6 1 70.84 6 2 68.36 6 3 81.21 6 4 0.88 6 5 10.00

————– Plane number 7 —————

Atoms Defining Plane Distance e.s.d. C16 (1) 0.0015 0.0030 C17 (1) -0.0124 0.0032 C18 (1) 0.0077 0.0029 C19 (1) 0.0037 0.0025 C20 (1) -0.0089 0.0022 C21 (1) 0.0087 0.0024

Mean deviation from plane is 0.0071 angstroms Chi-squared: 48.7

Dihedral angles between least-squares planes plane plane angle 7 1 68.84 7 2 66.39 7 3 79.68 7 4 1.19 7 5 10.72 7 6 2.06

————– Plane number 8 —————

Atoms Defining Plane Distance e.s.d. C12 (2) 0.0267 0.0021 C13 (2) 0.0177 0.0023 C14 (2) -0.0205 0.0026 C15 (2) -0.0198 0.0027 C16 (2) 0.0252 0.0030 C17 (2) 0.0337 0.0032 C18 (2) -0.0138 0.0029 C19 (2) -0.0311 0.0025 C20 (2) -0.0138 0.0022 C21 (2) -0.0035 0.0024

Mean deviation from plane is 0.0206 angstroms Chi-squared: 817.0

Dihedral angles between least-squares planes plane plane angle 8 1 29.56 8 2 27.27 8 3 10.29 8 4 71.09 8 5 80.54 8 6 71.72 8 7 70.30

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.9432 (1)0.2712 (3)0.4554 (1)0.0926 (8)
O20.9084 (1)0.5568 (3)0.5207 (1)0.0887 (8)
C10.7230 (1)0.0802 (4)0.4483 (1)0.0505 (8)
C20.6907 (1)0.2399 (4)0.3872 (1)0.0561 (9)
C30.6215 (2)0.3599 (5)0.3882 (1)0.065 (1)
C40.5852 (1)0.3281 (5)0.4489 (2)0.0623 (9)
C50.6171 (1)0.1754 (4)0.5108 (1)0.0502 (8)
C60.6854 (1)0.0520 (4)0.5093 (1)0.0524 (8)
C70.7960 (2)0.0554 (5)0.4502 (2)0.061 (1)
C80.8160 (2)0.2541 (5)0.4838 (2)0.066 (1)
C90.8931 (2)0.3666 (5)0.4859 (2)0.066 (1)
C100.7284 (2)0.2813 (5)0.3200 (2)0.085 (1)
C110.5786 (1)0.1459 (4)0.5782 (1)0.0542 (8)
C120.6040 (1)0.3214 (4)0.6453 (1)0.0469 (8)
C130.6612 (1)0.4832 (5)0.6471 (1)0.0566 (9)
C140.6828 (2)0.6481 (5)0.7091 (2)0.071 (1)
C150.6452 (2)0.6509 (5)0.7676 (2)0.075 (1)
C160.5440 (2)0.4906 (6)0.8278 (2)0.087 (1)
C170.4866 (2)0.3328 (7)0.8285 (2)0.094 (1)
C180.4681 (2)0.1594 (5)0.7706 (2)0.083 (1)
C190.5064 (2)0.1532 (5)0.7118 (1)0.064 (1)
C200.5654 (1)0.3179 (4)0.7083 (1)0.0505 (8)
C210.5853 (2)0.4885 (5)0.7685 (2)0.0596 (9)
H10.98670.32140.46260.111*0.500
H20.95170.60690.52780.106*0.500
H30.59750.47000.34500.078*
H40.53580.41590.44780.075*
H60.70850.05940.55230.063*
H70.834 (1)0.011 (4)0.425 (1)0.064 (8)*
H80.782 (1)0.343 (4)0.510 (1)0.083 (9)*
H10C0.73400.13770.29400.103*
H10A0.78330.35030.34280.103*
H10B0.69240.38270.27930.103*
H11A0.51810.15230.55390.065*
H11B0.59460.00270.60290.065*
H130.68810.48560.60440.068*
H140.72530.76100.70970.086*
H150.65990.76750.80990.089*
H160.55700.60910.86950.104*
H170.45780.33980.86960.112*
H180.42760.04280.77220.100*
H190.49270.03190.67120.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.082 (1)0.092 (2)0.128 (2)0.031 (1)0.067 (1)0.038 (1)
O20.075 (1)0.065 (1)0.139 (2)0.025 (1)0.052 (1)0.030 (1)
C10.050 (2)0.052 (2)0.055 (2)0.010 (1)0.024 (1)0.001 (1)
C20.058 (2)0.062 (2)0.053 (2)0.012 (2)0.024 (1)0.007 (2)
C30.067 (2)0.070 (2)0.061 (2)0.025 (2)0.023 (1)0.015 (2)
C40.058 (2)0.069 (2)0.063 (2)0.021 (2)0.023 (2)0.002 (2)
C50.052 (2)0.053 (2)0.050 (2)0.004 (2)0.022 (1)0.003 (1)
C60.053 (2)0.049 (2)0.056 (2)0.009 (1)0.018 (1)0.003 (1)
C70.057 (2)0.067 (2)0.066 (2)0.012 (2)0.029 (2)0.007 (2)
C80.057 (2)0.064 (2)0.088 (2)0.019 (2)0.037 (2)0.009 (2)
C90.063 (2)0.059 (2)0.084 (2)0.014 (2)0.033 (2)0.008 (2)
C100.096 (2)0.099 (3)0.075 (2)0.025 (2)0.046 (2)0.018 (2)
C110.057 (2)0.051 (2)0.060 (2)0.007 (1)0.026 (1)0.005 (2)
C120.045 (2)0.046 (2)0.046 (2)0.010 (1)0.010 (1)0.001 (1)
C130.051 (2)0.060 (2)0.056 (2)0.003 (2)0.014 (1)0.002 (2)
C140.067 (2)0.062 (2)0.071 (2)0.007 (2)0.002 (2)0.004 (2)
C150.081 (2)0.072 (2)0.060 (2)0.002 (2)0.006 (2)0.020 (2)
C160.099 (3)0.107 (3)0.056 (2)0.024 (2)0.026 (2)0.015 (2)
C170.100 (3)0.132 (4)0.062 (2)0.024 (3)0.044 (2)0.004 (2)
C180.088 (2)0.097 (3)0.077 (2)0.003 (2)0.044 (2)0.004 (2)
C190.074 (2)0.067 (2)0.061 (2)0.004 (2)0.033 (2)0.002 (2)
C200.052 (2)0.051 (2)0.048 (2)0.016 (1)0.015 (1)0.002 (1)
C210.060 (2)0.066 (2)0.050 (2)0.015 (2)0.012 (1)0.006 (2)
Geometric parameters (Å, º) top
O1—C91.263 (3)C10—H10B0.98
O1—H10.77C11—C121.517 (3)
O2—C91.267 (3)C11—H11A0.98
O2—H20.77C11—H11B0.98
C1—C21.396 (3)C12—C131.357 (3)
C1—C61.399 (3)C12—C201.432 (3)
C1—C71.468 (3)C13—C141.411 (3)
C2—C31.376 (3)C13—H130.98
C2—C101.510 (3)C14—C151.353 (3)
C3—C41.383 (3)C14—H140.98
C3—H30.98C15—C211.403 (3)
C4—C51.377 (3)C15—H150.98
C4—H40.98C16—C171.352 (4)
C5—C61.377 (3)C16—C211.410 (3)
C5—C111.510 (3)C16—H160.98
C6—H60.98C17—C181.401 (4)
C7—C81.311 (3)C17—H170.98
C7—H70.96 (2)C18—C191.364 (3)
C8—C91.459 (3)C18—H180.98
C8—H81.00 (2)C19—C201.413 (3)
C10—H10C0.98C19—H190.98
C10—H10A0.98C20—C211.415 (3)
C9—O1—H1119.6C5—C11—H11A108.1
C9—O2—H2117.7C5—C11—H11B108.1
C2—C1—C6119.1 (2)C12—C11—H11A108.1
C2—C1—C7121.2 (2)C12—C11—H11B108.1
C6—C1—C7119.7 (2)H11A—C11—H11B109.5
C1—C2—C3118.5 (2)C11—C12—C13122.3 (2)
C1—C2—C10122.1 (2)C11—C12—C20118.8 (2)
C3—C2—C10119.4 (2)C13—C12—C20118.9 (2)
C2—C3—C4121.3 (2)C12—C13—C14121.5 (2)
C2—C3—H3119.3C12—C13—H13119.2
C4—C3—H3119.4C14—C13—H13119.2
C3—C4—C5121.2 (2)C13—C14—C15120.2 (3)
C3—C4—H4119.4C13—C14—H14119.9
C5—C4—H4119.4C15—C14—H14119.9
C4—C5—C6117.7 (2)C14—C15—C21120.7 (3)
C4—C5—C11121.0 (2)C14—C15—H15119.7
C6—C5—C11121.4 (2)C21—C15—H15119.6
C1—C6—C5122.2 (2)C17—C16—C21121.4 (3)
C1—C6—H6118.9C17—C16—H16119.3
C5—C6—H6118.9C21—C16—H16119.3
C1—C7—C8127.0 (3)C16—C17—C18120.3 (3)
C1—C7—H7116 (1)C16—C17—H17119.8
C8—C7—H7117 (1)C18—C17—H17119.8
C7—C8—C9121.8 (3)C17—C18—C19119.9 (3)
C7—C8—H8125 (1)C17—C18—H18120.1
C9—C8—H8113 (1)C19—C18—H18120.1
O1—C9—O2122.2 (3)C18—C19—C20121.3 (3)
O1—C9—C8119.9 (3)C18—C19—H19119.3
O2—C9—C8117.9 (3)C20—C19—H19119.3
C2—C10—H10C109.5C12—C20—C19122.6 (3)
C2—C10—H10A109.5C12—C20—C21119.1 (2)
C2—C10—H10B109.5C19—C20—C21118.2 (2)
H10C—C10—H10A109.4C15—C21—C16121.7 (3)
H10C—C10—H10B109.4C15—C21—C20119.4 (2)
H10A—C10—H10B109.4C16—C21—C20118.8 (3)
C5—C11—C12114.9 (2)
O1—C9—C8—C70.8 (5)C11—C12—C13—C14178.7 (2)
O2—C9—C8—C7178.9 (3)C11—C12—C20—C192.0 (3)
C1—C2—C3—C41.4 (4)C11—C12—C20—C21176.5 (2)
C1—C6—C5—C41.0 (4)C12—C13—C14—C151.4 (4)
C1—C6—C5—C11178.7 (2)C12—C20—C19—C18177.2 (2)
C1—C7—C8—C9176.2 (3)C12—C20—C21—C153.1 (4)
C2—C1—C6—C50.5 (4)C12—C20—C21—C16176.8 (2)
C2—C1—C7—C8155.1 (3)C13—C12—C20—C19178.9 (2)
C2—C3—C4—C50.2 (4)C13—C12—C20—C212.7 (3)
C3—C2—C1—C61.7 (4)C13—C14—C15—C211.1 (4)
C3—C2—C1—C7179.2 (2)C14—C13—C12—C200.5 (4)
C3—C4—C5—C61.3 (4)C14—C15—C21—C16178.7 (3)
C3—C4—C5—C11178.4 (2)C14—C15—C21—C201.2 (4)
C4—C3—C2—C10179.7 (3)C15—C21—C16—C17179.6 (3)
C4—C5—C11—C1280.7 (3)C15—C21—C20—C19178.4 (2)
C5—C6—C1—C7179.7 (2)C16—C17—C18—C191.8 (5)
C5—C11—C12—C134.2 (3)C16—C21—C20—C191.7 (4)
C5—C11—C12—C20175.0 (2)C17—C16—C21—C200.5 (5)
C6—C1—C2—C10179.4 (2)C17—C18—C19—C200.6 (5)
C6—C1—C7—C825.8 (4)C18—C17—C16—C211.3 (5)
C6—C5—C11—C1298.9 (3)C18—C19—C20—C211.2 (4)
C7—C1—C2—C100.3 (4)
Selected geometric parameters (Å, °) [using atom labelling as for (I)] for the propenoic acid moiety in three trans-cinnamic acids: (I), the title compound; (II), 4-methyl-trans-cinnamic acid (Kashino et al., 1989); (III), trans-cinnamic acid (Bryan &amp; Freyberg, 1975). top
Parameter(I)(II)(III)
C1-C71.468 (3)1.458 (4)1.467 (4)
C7-C81.311 (3)1.315 (4)1.322 (4)
C8-C91.459 (3)1.458 (4)1.470 (4)
C9-O11.263 (3)1.274 (4)1.279 (4)
C9-O21.267 (3)1.255 (4)1.259 (4)
C1-C7-C8127.0 (3)127.4 (3)126.2 (3)
C7-C8-C9121.8 (3)123.1 (3)122.3 (3)
C8-C9-O1119.9 (3)118.8 (3)122.7 (3)
C8-C9-O2117.9 (3)118.8 (3)118.6 (3)
O1-C9-O2122.2 (3)122.4 (3)122.7 (3)
 

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